Skip to main content
. Author manuscript; available in PMC: 2011 Jan 14.
Published in final edited form as: J Am Chem Soc. 2008 Jun 17;130(27):8726–8732. doi: 10.1021/ja800250q

Table 2.

Solvent-dependent E/Z selectivities11 for enolization by LiHMDS (eq 5).a

E/Z selectivity
R
 Et3N/tolueneb
 THFc
Et 140:1 1:411a
i-pr (3) 100:1 1:1411a
Cy 80:1 1:3010
Ph 3.5:1 1:>10011a
CH3O 22:1 1:1211b,k
graphic file with name nihms56225t1.jpg 50:1 1:811c,d
a

[ketone] = 0.05 M; [LiHMDS] = 0.15 M.

b

[Et3N] = 1.5 M in toluene; −78 °C.

c

Neat THF.